(2S,3R,4S)-3-ethyl-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-carbonitrile

Base Information

Chemical Name:(2S,3R,4S)-3-ethyl-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-carbonitrile
CAS No.:1433543-86-2
Molecular Formula:C₁₉H₁₉N₃O₄S
Molecular Weight:385.444
Hs Code.:

Synonyms:(2S,3R,4S)-3-ethyl-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-carbonitrile

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Chemical Property of (2S,3R,4S)-3-ethyl-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-carbonitrile

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Technology Process of (2S,3R,4S)-3-ethyl-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-carbonitrile

There total 6 articles about (2S,3R,4S)-3-ethyl-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-carbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

: 7677-24-9
trimethylsilyl cyanide

: (3R,4S)-3-ethyl-2-methoxy-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine

: 1433543-86-2
(2S,3R,4S)-3-ethyl-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-carbonitrile

Guidance literature:: With boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 12h; stereoselective reaction;
DOI:10.1002/chem.201202409

Reference yield:

: 102-96-5
(2-nitroethenyl)benzene

: 1433543-86-2
(2S,3R,4S)-3-ethyl-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-carbonitrile

Guidance literature:: Multi-step reaction with 6 steps

1: L-proline / dimethyl sulfoxide / 12 h / 25 °C / Sealed tube

2: toluene-4-sulfonic acid / toluene / 20 h / Reflux; Inert atmosphere

3: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / -20 - 0 °C

4: triethylamine / dichloromethane / 12 h / 0 - 20 °C

5: camphor-10-sulfonic acid / methanol / 8 h / 20 °C

6: boron trifluoride diethyl etherate / acetonitrile / 12 h / 0 °C

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; triethylamine; L-proline; In methanol; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; 1: |Michael Addition;
DOI:10.1002/chem.201202409

Reference yield:

: 1433543-43-1
2-((2S,3R)-1-nitro-2-phenylpentan-3-yl)-1,3-dioxolane

: 1433543-86-2
(2S,3R,4S)-3-ethyl-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-carbonitrile

Guidance literature:: Multi-step reaction with 4 steps

1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / -20 - 0 °C

2: triethylamine / dichloromethane / 12 h / 0 - 20 °C

3: camphor-10-sulfonic acid / methanol / 8 h / 20 °C

4: boron trifluoride diethyl etherate / acetonitrile / 12 h / 0 °C

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; triethylamine; In methanol; dichloromethane; acetonitrile;
DOI:10.1002/chem.201202409